(R)-6-[(1E,3Z,7E,9E)-(5R,14R)-14-(tert-Butyl-dimethyl-silanyloxy)-3-ethyl-5,9-dimethyl-12-(tetrahydro-pyran-2-yloxy)-heptadeca-1,3,7,9-tetraenyl]-5,6-dihydro-pyran-2-one | 331814-85-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (R)-6-[(1E,3Z,7E,9E)-(5R,14R)-14-(tert-Butyl-dimethyl-silanyloxy)-3-ethyl-5,9-dimethyl-12-(tetrahydro-pyran-2-yloxy)-heptadeca-1,3,7,9-tetraenyl]-5,6-dihydro-pyran-2-one
• CAS: 331814-85-8
• 化学式: C₃₇H₆₂O₅Si
• 分子量: 614.982
• InChiKey: ICGMZBJNQVBLEY-HPFVHUHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.16
• 重原子数：
  43.0
• 可旋转键数：
  17.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-6-[(1E,3Z,7E,9E)-(5R,14R)-14-(tert-Butyl-dimethyl-silanyloxy)-3-ethyl-5,9-dimethyl-12-(tetrahydro-pyran-2-yloxy)-heptadeca-1,3,7,9-tetraenyl]-5,6-dihydro-pyran-2-one 在 4-甲基苯磺酸吡啶 作用下， 以 叔丁醇 为溶剂， 反应 18.0h， 以100%的产率得到(R)-6-[(1E,3Z,7E,9E)-(5R,14R)-14-(tert-Butyl-dimethyl-silanyloxy)-3-ethyl-12-hydroxy-5,9-dimethyl-heptadeca-1,3,7,9-tetraenyl]-5,6-dihydro-pyran-2-one
  参考文献：
  名称：

  Participation of the β-hydroxyketone part for potent cytotoxicity of callystatin A, a spongean polyketide

  摘要：

  The participation of the beta -hydroxyketone part of callystatin A in the potent cytotoxicity was analyzed through the analogue-syntheses and the assessment of their biological potencies. The ketonic carbonyl, the 19-hydroxyl, and the three asymmetric methyl groups located in the beta -hydroxyketone part of callystatin A were revealed to contribute to the cytotoxic potency, respectively. Moreover, the alpha,beta -unsaturated delta -lactone portion was shown to serve as a conclusive functional group for the cytotoxic activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00220-0
• 作为产物：
  描述：

  (R)-3-hydroxy-N-methoxy-N-methylhexanamide 在 2,6-二甲基吡啶 、 sodium periodate 、 四氧化锇 、 正丁基锂 、 四溴化碳 、 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 、 二甲基亚砜 、 N-甲基吗啉氧化物 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 丙酮 、 甲苯 、 乙腈 为溶剂， 反应 198.5h， 生成 (R)-6-[(1E,3Z,7E,9E)-(5R,14R)-14-(tert-Butyl-dimethyl-silanyloxy)-3-ethyl-5,9-dimethyl-12-(tetrahydro-pyran-2-yloxy)-heptadeca-1,3,7,9-tetraenyl]-5,6-dihydro-pyran-2-one
  参考文献：
  名称：

  Participation of the β-hydroxyketone part for potent cytotoxicity of callystatin A, a spongean polyketide

  摘要：

  The participation of the beta -hydroxyketone part of callystatin A in the potent cytotoxicity was analyzed through the analogue-syntheses and the assessment of their biological potencies. The ketonic carbonyl, the 19-hydroxyl, and the three asymmetric methyl groups located in the beta -hydroxyketone part of callystatin A were revealed to contribute to the cytotoxic potency, respectively. Moreover, the alpha,beta -unsaturated delta -lactone portion was shown to serve as a conclusive functional group for the cytotoxic activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00220-0